Casopitant

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Casopitant
Accession Number
DB06634
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
679769 / GW-679769 / GW679769
Product Ingredients
IngredientUNIICASInChI Key
Casopitant mesylate7VSV9BL497414910-30-8YRFKYVWDPCOSTE-REWBLLDVSA-N
International/Other Brands
Rezonic / Zunrisa
Categories
UNII
3B03KPM27L
CAS number
414910-27-3
Weight
Average: 616.625
Monoisotopic: 616.264823524
Chemical Formula
C30H35F7N4O2
InChI Key
XGGTZCKQRWXCHW-WMTVXVAQSA-N
InChI
InChI=1S/C30H35F7N4O2/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3/t19-,25+,27-/m1/s1
IUPAC Name
(2R,4S)-4-(4-acetylpiperazin-1-yl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide
SMILES
C[C@@H](N(C)C(=O)N1CC[C@@H](C[C@@H]1C1=CC=C(F)C=C1C)N1CCN(CC1)C(C)=O)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

Pharmacology

Indication

Investigated for use/treatment in urinary incontinence and adverse effects (chemotherapy).

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytochrome P450 3A4Not AvailableHumans
USubstance-P receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
8092668
BindingDB
50336575
ChEBI
135967
ChEMBL
CHEMBL1672054
PharmGKB
PA166129533
Wikipedia
Casopitant
ATC Codes
A04AD13 — Casopitant

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticSocial Anxiety Disorder (SAD)1
1CompletedPreventionChemotherapy-Induced Nausea and Vomiting (CINV) / Healthy Volunteers2
1CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Healthy Volunteers2
1CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Malignancies1
1CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Post-Operative Nausea and Vomiting (PONV)1
1CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Vomiting1
1CompletedTreatmentImpaired Renal Function / Vomiting2
1TerminatedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Malignancies1
2CompletedDiagnosticSleep Initiation and Maintenance Disorders / Sleeplessness1
2CompletedPreventionNausea and Vomiting, Postoperative / Post-Operative Nausea and Vomiting (PONV)1
2CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV)1
2CompletedTreatmentChemotherapy-Induced / Nausea and vomiting1
2CompletedTreatmentFunctional Dyspepsia / Nonulcer Dyspepsia1
2CompletedTreatmentIncontinence, Urinary and Urinary Bladder, Overactive / Urinary Bladder, Overactive1
2CompletedTreatmentMajor Depressive Disorder (MDD)2
2CompletedTreatmentSleep Initiation and Maintenance Disorders / Sleeplessness3
2TerminatedTreatmentIncontinence, Urinary and Urinary Bladder, Overactive / Urinary Bladder, Overactive1
3CompletedPreventionChemotherapy-Induced Nausea and Vomiting (CINV) / Nausea / Vomiting1
3CompletedPreventionNausea and Vomiting, Postoperative / Post-Operative Nausea and Vomiting (PONV)2
3CompletedSupportive CareChemotherapy-Induced Nausea and Vomiting (CINV) / Nausea and vomiting1
3CompletedTreatmentChemotherapy-Induced Nausea and Vomiting (CINV) / Nausea / Vomiting1
3WithdrawnSupportive CareChemotherapy-Induced Nausea and Vomiting (CINV) / Malignancies / Nausea and vomiting / Solid Tumor Cancers1
Not AvailableCompletedNot AvailableDepression / Depressive Disorders / Fibromyalgia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00445 mg/mLALOGPS
logP4.73ALOGPS
logP4.97ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)7.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.1 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity149.02 m3·mol-1ChemAxon
Polarizability57.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Trifluoromethylbenzenes / Piperidinecarboxamides / Aminopiperidines / Aralkylamines / Toluenes / Fluorobenzenes / N-alkylpiperazines / Aryl fluorides / Tertiary carboxylic acid amides / Acetamides
show 10 more
Substituents
Phenylpiperidine / Trifluoromethylbenzene / 1-piperidinecarboxamide / Piperidinecarboxamide / 4-aminopiperidine / Fluorobenzene / Halobenzene / Toluene / N-alkylpiperazine / Aralkylamine
show 29 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Motta P, Pons N, Pagliarusco S, Pellegatti M, Bonomo F: Casopitant: in vitro data and SimCyp simulation to predict in vivo metabolic interactions involving cytochrome P450 3A4. Drug Metab Dispos. 2011 Mar;39(3):363-72. doi: 10.1124/dmd.110.035071. Epub 2010 Dec 13. [PubMed:21149541]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tachykinin receptor activity
Specific Function
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of aff...
Gene Name
TACR1
Uniprot ID
P25103
Uniprot Name
Substance-P receptor
Molecular Weight
46250.5 Da
References
  1. Di Fabio R, Alvaro G, Griffante C, Pizzi DA, Donati D, Mattioli M, Cimarosti Z, Guercio G, Marchioro C, Provera S, Zonzini L, Montanari D, Melotto S, Gerrard PA, Trist DG, Ratti E, Corsi M: Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2- methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate. J Med Chem. 2011 Feb 24;54(4):1071-9. doi: 10.1021/jm1013264. Epub 2011 Jan 13. [PubMed:21229983]

Drug created on March 19, 2008 10:42 / Updated on August 02, 2019 07:53